3-Methoxy-benzaldehyde thio-semi-carbazone.

The title compound, C(9)H(11)N(3)OS, was prepared by the reaction of 3-methoxy-benzaldehyde and thio-semicarbazide. The benzyl-idene ring and the thio-semicarbazone fragment are slightly twisted, making a dihedral angle of 14.1 (1)°. A weak intra-molecular N-H⋯N hydrogen bond may influence the conformation of the mol-ecule. Inter-molecular N-H⋯S hydrogen bonds build up a three-dimensional network.

Related literature

For a general background to thio­semicarbazone compounds, see: Casas et al. (2000 ▶); Tarafder et al. (2000 ▶); Ferrari et al. (2000 ▶); Deschamps et al. (2003 ▶); Maccioni et al. (2003 ▶); Chimenti et al.(2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C9H11N3OS

M = 209.27

Monoclinic,

a = 11.814 (2) Å

b = 5.6760 (11) Å

c = 15.248 (3) Å

β = 90.29 (3)°

V = 1022.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.908, T max = 0.969

1946 measured reflections

1852 independent reflections

1494 reflections with I > 2σ(I)

R int = 0.017

3 standard reflections every 200 reflections intensity decay: 9%

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.06

1852 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901040X/dn2432sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901040X/dn2432Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H11N3OS	F(000) = 440
Mr = 209.27	Dx = 1.359 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 27 reflections
a = 11.814 (2) Å	θ = 1–25°
b = 5.6760 (11) Å	µ = 0.29 mm−1
c = 15.248 (3) Å	T = 293 K
β = 90.29 (3)°	Block, colorless
V = 1022.5 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1494 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.017
graphite	θmax = 25.3°, θmin = 1.7°
ω/2θ scans	h = −14→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→6
Tmin = 0.908, Tmax = 0.969	l = −18→18
1946 measured reflections	3 standard reflections every 200 reflections
1852 independent reflections	intensity decay: 9%

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0521P)2 + 0.3815P] where P = (Fo2 + 2Fc2)/3
1852 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.51511 (6)	1.47619 (10)	0.35880 (3)	0.0442 (2)
O1	0.85492 (14)	0.6407 (3)	0.83956 (9)	0.0496 (5)
N1	0.66878 (15)	1.0213 (3)	0.50804 (11)	0.0369 (4)
N2	0.60984 (16)	1.2149 (3)	0.47967 (11)	0.0407 (5)
H2	0.5936	1.3268	0.5155	0.049*
N3	0.59915 (18)	1.0451 (4)	0.34546 (12)	0.0497 (5)
H3A	0.6324	0.9237	0.3674	0.060*
H3B	0.5800	1.0463	0.2910	0.060*
C1	0.9085 (2)	0.4449 (6)	0.88050 (16)	0.0614 (8)
H1A	0.9862	0.4377	0.8627	0.092*
H1B	0.8706	0.3024	0.8634	0.092*
H1C	0.9049	0.4624	0.9430	0.092*
C2	0.84356 (18)	0.6327 (4)	0.75008 (14)	0.0383 (5)
C3	0.77906 (17)	0.8120 (4)	0.71427 (13)	0.0366 (5)
H3	0.7479	0.9264	0.7505	0.044*
C4	0.76070 (17)	0.8221 (4)	0.62447 (13)	0.0350 (5)
C5	0.8097 (2)	0.6510 (4)	0.57024 (14)	0.0428 (6)
H5	0.7982	0.6566	0.5099	0.051*
C6	0.8741 (2)	0.4764 (4)	0.60621 (16)	0.0503 (6)
H6	0.9071	0.3642	0.5700	0.060*
C7	0.8914 (2)	0.4638 (4)	0.69715 (16)	0.0472 (6)
H7	0.9346	0.3430	0.7214	0.057*
C8	0.69256 (18)	1.0136 (4)	0.58932 (13)	0.0379 (5)
H8	0.6663	1.1311	0.6265	0.045*
C9	0.57769 (17)	1.2279 (4)	0.39499 (13)	0.0332 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0643 (4)	0.0374 (3)	0.0309 (3)	0.0090 (3)	−0.0081 (3)	0.0035 (2)
O1	0.0534 (10)	0.0621 (12)	0.0333 (8)	0.0106 (9)	−0.0062 (7)	0.0109 (8)
N1	0.0429 (10)	0.0363 (10)	0.0315 (9)	0.0058 (9)	−0.0045 (8)	0.0024 (8)
N2	0.0555 (12)	0.0378 (11)	0.0286 (9)	0.0118 (9)	−0.0091 (8)	−0.0020 (8)
N3	0.0732 (14)	0.0442 (12)	0.0315 (9)	0.0164 (11)	−0.0128 (9)	−0.0056 (9)
C1	0.0631 (16)	0.077 (2)	0.0444 (14)	0.0194 (15)	−0.0057 (12)	0.0225 (14)
C2	0.0335 (11)	0.0471 (14)	0.0343 (11)	−0.0031 (10)	−0.0041 (9)	0.0072 (10)
C3	0.0338 (11)	0.0429 (13)	0.0331 (11)	0.0020 (10)	0.0002 (9)	0.0024 (10)
C4	0.0331 (11)	0.0380 (12)	0.0340 (11)	−0.0035 (10)	−0.0043 (9)	0.0045 (10)
C5	0.0526 (14)	0.0413 (14)	0.0346 (11)	0.0013 (11)	−0.0061 (10)	−0.0020 (10)
C6	0.0622 (16)	0.0432 (14)	0.0454 (13)	0.0109 (12)	−0.0051 (12)	−0.0084 (11)
C7	0.0517 (14)	0.0401 (13)	0.0497 (14)	0.0076 (11)	−0.0091 (11)	0.0061 (11)
C8	0.0389 (11)	0.0439 (13)	0.0309 (11)	0.0039 (10)	−0.0012 (9)	0.0002 (10)
C9	0.0372 (11)	0.0357 (12)	0.0266 (10)	−0.0032 (10)	−0.0024 (8)	0.0015 (9)

S1—C9	1.683 (2)	C2—C7	1.377 (3)
O1—C2	1.371 (2)	C2—C3	1.382 (3)
O1—C1	1.422 (3)	C3—C4	1.386 (3)
N1—C8	1.270 (3)	C3—H3	0.9300
N1—N2	1.370 (2)	C4—C5	1.402 (3)
N2—C9	1.346 (3)	C4—C8	1.454 (3)
N2—H2	0.8600	C5—C6	1.363 (3)
N3—C9	1.309 (3)	C5—H5	0.9300
N3—H3A	0.8600	C6—C7	1.402 (3)
N3—H3B	0.8600	C6—H6	0.9300
C1—H1A	0.9600	C7—H7	0.9300
C1—H1B	0.9600	C8—H8	0.9300
C1—H1C	0.9600
C2—O1—C1	116.9 (2)	C4—C3—H3	119.9
C8—N1—N2	116.44 (18)	C3—C4—C5	119.4 (2)
C9—N2—N1	119.16 (18)	C3—C4—C8	118.6 (2)
C9—N2—H2	120.4	C5—C4—C8	122.00 (19)
N1—N2—H2	120.4	C6—C5—C4	119.8 (2)
C9—N3—H3A	120.0	C6—C5—H5	120.1
C9—N3—H3B	120.0	C4—C5—H5	120.1
H3A—N3—H3B	120.0	C5—C6—C7	120.9 (2)
O1—C1—H1A	109.5	C5—C6—H6	119.6
O1—C1—H1B	109.5	C7—C6—H6	119.6
H1A—C1—H1B	109.5	C2—C7—C6	119.1 (2)
O1—C1—H1C	109.5	C2—C7—H7	120.5
H1A—C1—H1C	109.5	C6—C7—H7	120.5
H1B—C1—H1C	109.5	N1—C8—C4	120.3 (2)
O1—C2—C7	124.6 (2)	N1—C8—H8	119.8
O1—C2—C3	114.8 (2)	C4—C8—H8	119.8
C7—C2—C3	120.6 (2)	N3—C9—N2	117.1 (2)
C2—C3—C4	120.2 (2)	N3—C9—S1	124.11 (16)
C2—C3—H3	119.9	N2—C9—S1	118.78 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···S1i	0.86	2.57	3.370 (2)	156
N3—H3B···S1ii	0.86	2.57	3.411 (2)	166
N3—H3A···N1	0.86	2.25	2.611 (3)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯S1i	0.86	2.57	3.370 (2)	156
N3—H3B⋯S1ii	0.86	2.57	3.411 (2)	166
N3—H3A⋯N1	0.86	2.25	2.611 (3)	105

Symmetry codes: (i) ; (ii) .